Martin Trávníček

A New Routine for the Synthesis of N-substituted-N-(sulfonyl) bromoacetamides with ZnCl2 as a Catalyst

A series of N-acylated N-substituted sulfonamides was prepared for the first time in good yields and with excellent conversion by the reaction of N-substituted-N-(p-toluene) sulfonamides (1) with acetyl chloride and bromoacetyl bromide (2), respectively, in the presence of a catalytic amount of anhydrous ZnCl2.

STEREOCHEMISTRY OF 1,3-DIPOLAR CYCLOADDITION REACTION OF AZOMETHINE YLIDES DERIVED FROM N-ALKYL-N-(4-TOLUENESULPHONYL) CARBAMOYLMETHYL PHENANTHRIDINIUM WITH OLEFINIC DIPOLAROPHILES

A series of prepared N-alkyl-N-(p-toluenesulfonyl) bromoacetamides afforded with phenanthridine quarternary phenanthridinium salts. These when treated with triethylamine in dichloromethane form azomethine ylides that undergo cyclization reaction with present activated olefinic double bond. This way pyrrolidino[1,2-f]phenanthridines can be obtained. Their stereochemistry was studied. Some of them were separated on non-racemic cellulose based sorbents with CD detection.